DE3315806A1 - PHENOXYTRIAZOLYL KETONES AND CARBINOLS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES - Google Patents

Description

BAYER AKTIENGESELLSCHAFT 5090 Leverkusen, Bayerwerk Zentralbereich 2 0.04

Patents, trademarks and licenses Slr / Ke

Yes

Phenoxytriazolyl ketones and carbinols, process for their Manufacture and their use as fungicides

The present application relates to new phenoxytriazolyl ketones and carbinols, a process for their preparation and their use as fungicides.

It has already become known that certain phenoxytriazolyl ketones and carbinols, such as, for example, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) -2-butanone , 1- (4-bromophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) -2-butanol or 1- (2,6-dichlorophenoxy) -2-pheny1- 1- (1,2,4-triazol-1-yl) -2-ethanone, generally have good fungicidal properties (compare OE-PS 22 01 063 CLeA 14 118] and DE-PS 23 24 010 CLeA 14 9713). It is also already known that zinc ethylene-1,2-bisdithiocarbamidate is a good agent for combating fungal plant diseases (see Phytopathology 33 , 1113 (1963)). However, the action of these compounds is not always completely satisfactory in certain areas of indication, especially when low amounts and concentrations are used.

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There were new PhenoxytriazoLyL ketones and carbinols the general formula

RO - (Cj) ' 0 - CH - A - C (CH ₃ ) ₃ (I)

Π N

N Ll

in which

A stands for the keto group or the CH (OH) group and

R for hydrogen, alkenyl, alkynyl, haloalkyl, haloalkenyl, AlkylcarbonyI, optionally substituted Benzyl or optionally substituted phenoxymethyl L stands,

and their acid addition salts and metal salt complexes found.

Those compounds of formula (I) in which A for the CH (OH) group has two asymmetric ones ] 5 carbon atoms; they can therefore be in the two geometrical Isomers (threo and erythro form) are present, which occur in different proportions can. In both cases they exist as optical isomers.

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It has also been found that one obtains the phenoxytriazo LyL-ketones and -carbinoLs of the general formula (I), if you HaLogen-triazo LyL-pinakoLiη der FormeL

HaL - CH - CO - C (CH ₃ ) ₃ (II)

'n ^; _J

in which

HaL stands for fluorine, chlorine or bromine,

with phenols of the formula

R-O - <(J) -OH (III)

in which

R has the meaning given above,

in the presence of a diluent and in the presence of an acid binding agent; and if necessary, the keto derivatives obtained in this way Formula (I) reduced in the usual way by known methods.

If necessary, an acid or a metal salt can then be added to the compounds of formula (I) obtained in this way.

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The new Phenoxytriazo LyL ketones and carbinols der Formula (I) have strong fungicidal properties. The compounds according to the invention surprisingly show a better fungicidal activity than the compounds known from the prior art 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) -2-butanone, 1- (4-bromophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) -2-butanol and 1- (2,6-dichlorophenoxy) -2-pheny 1-1- (1,2,4-triazol-1-yI) -2-ethanone, which constitutionally and effectively obvious compounds are, and recognized as the Zinket hy len-1,2-bisdithio-carbamidate, which is a is a good means of the same direction of action. The according to the invention Fabrics thus enrich technology.

The Phenoxytriazo Iy l-ketones and carbinols according to the invention are generally defined by the formula (I). In this Formula R preferably represents hydrogen, straight-chain or branched alkenyl with 2 to 18 carbon atoms, straight chain or branched alkynyl 'with 2 to 6 carbon atoms, Haloalkyl with 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, such as Fluorine and chlorine atoms, haloalkene with 2 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, and for each optionally in the phenyl part one to three times, the same or differently substituted benzyl or phenoxymethyl, being mentioned as substituents: halogen, alkyl with 1 to 2 carbon atoms, nitro and haloalkyl with 1 to 2 carbon atoms and 1 to 5 same or different Halogen atoms such as fluorine and chlorine atoms.

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Those compounds of the formula (I) in which R is hydrogen, straight-chain, are particularly preferred or branched alkenyl with 3 to 12 carbon atoms, straight-chain or branched alkynyl with 3 to 4 carbon atoms, Trifluoromethy L, substituted by chlorine ALkenyL with 3 or 4 carbon atoms, acetyl, ethylcarbonyl as well as for each optionally in the phenyl part benzyl or phenoxymethy L substituted once or twice, identically or differently, where aLs are substituents the following may be mentioned: fluorine, chlorine and methyl.

For example, if 1-bromo-3,3 ~ dimet hy 1-1 (1 , 2,4-triazol-1-y I) -butan-2-one and 4-A I IyLoxyphenoI aLs Starting materials, the course of the reaction can be as follows Formula scheme can be reproduced:

Br-CH-CO-C (CHO ₃

/ Nn _n + CH ₂ = CH-CH ₂ -O-aj; -ÖH

N ¹ y

= CH-CH ₂ -0- <U) -0-CH-C0-C (CH ₃ ) ₃

If, for example, 1 - (4-ALLyLoxyphenoxy) -3,3-dimet is used hyL-1- (1,2,4-triazoL-1-yL) -2-butanone and sodium borohydride As starting materials, the course of the reduction reaction can be repeated using the following formula:

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are given:

CH ₂ = CH-CH ₂ -OU ^ / -0-CH-CO-C (CH ₃ ) ₃

OH

■ O-CH-CH-C (CH ₃ ) ₃

N U

When carrying out the method according to the invention a Ls starting materials to be used Halogen-triazolylpinakoLine are generally defined by the formula (II). In this formula, shark preferably stands for those in the Invention definition given meanings.

The halotriazolyl-pinacolines of the formula (II) are be-.10 (compare DE-OS 27 56 269 CLeA 18 5653, and DE-OS 29 37 595 CLeA 19 9343). You can be obtained afterwards by adding Triazo IylpinakoIiη of the formula

H ₂ C - CO - C (CH ₃ ) ₃ (IV)

N W

with bromine or chlorine in the presence of a solvent and in the presence of a hydrogen halide acceptor and optionally in the bromine (chlorine) triazo IyI-pinacolin obtained the bromine (chlorine) exchanges for fluorine in the usual way.

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The also for the process according to the invention as starting materials Phenols to be used are generally defined by the formula (III), in this formula R stands preferably for those meanings that already exist in Connection with the description of the erfindunsggemäße Substances of the formula (I) mentioned preferably for this radical became.

The phenols of formula (III) are generally known Verbin eiungen of organic chemistry, or they can be obtained in IQ generally customary manner.

Suitable diluents for the implementation according to the invention are preferably inert organic solvents. These preferably include ethers, such as diethyl ether; Alcohols such as methanol; Ketones such as acetone; aromatic Hydrocarbons such as benzene; as well as dimethyl sulfoxide and dimethylformamide.

The inventive reaction is in the presence of a Acid binder made. One can usually do all of them usable inorganic or organic acid binders add, such as alkali metal carbonates, for example potassium carbonate or sodium carbonate, alkali metal hydroxides, for example sodium hydroxide, alkali metal alcoholates, or such as lower tertiary alkylamines, for example Triethylamine.

When carrying out the process according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the temperature is between 0 and 140 ^° C., preferably between 50 and 100 ^° C.

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When carrying out the method according to the invention 1 to 4 mol of phenol of the formula (III) are preferably used for 1 mol of the compound of the formula (II). the Isolation of the compounds of formula (I) takes place in usual way.

The reduction according to the invention takes place in the usual way, e.g. by reaction with complex hydrides, optionally in the presence of a diluent, or by Reaction with aluminum isopropylate in the presence of a Diluent.

When working with complex hydrides, polar organic solvents are suitable as diluents for the reaction according to the invention. These preferably include alcohols such as methanol, ethanol, butanol, isopropanol and ethers such as diethyl ether or tetrahydrofuran. The reaction is generally carried out at from 0 to 30 ^° C., preferably from 0 to 20 ^° C. For this purpose, about 1 mol of a complex hydride, such as sodium borohydride or lithium alanate, is used for 1 mol of the ketone of the formula (I).

For isolating the reduced compounds of the formula

(I) the residue is taken up in dilute hydrochloric acid, then made alkaline and with an organic Solvent extracted. Further work-up is carried out in the customary manner.

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If aluminum isopropylate is used, the preferred diluents for the reaction according to the invention are alcohols, such as isopropanol, or inert hydrocarbons, such as benzene. The reaction temperatures can in turn be varied within a relatively wide range; In general, the temperature is between 20 and 120 ^° C., preferably at 50 to 100 ^° C. To carry out the reaction, about 0.3 to 2 mol of aluminum isopropyl lat is employed per mole of the ketone of the formula (I). To isolate the reduced compounds of the formula (I), the excess solvent is removed in vacuo and the resulting aluminum compounds are decomposed with dilute sulfuric acid or sodium hydroxide solution. The further work-up takes place in the customary manner.

For the preparation of physiologically acceptable acid addition salts of the compounds of the formula (I) come voi- preferably the following acids: hydrohalic acids, such as hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, Nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as acetic acid, Maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid, lactic acid, and sulfonic acids such as p-toluenesulfonic acid and 1,5-naphtha Iin- disuI fonsäure *

The acid addition salts of the compounds of the formula (I) can in a simple manner by customary salt formation methods, such as by dissolving a compound of the formula (I) in a suitable inert solvent and adding

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of the acid such as hydrochloric acid and known in the art Way, e.g. by filtering off, isolated and, if necessary, Ls Washing purified with an inert organic solvent will"

For the preparation of metal salt complexes of the compounds of the formula (I), salts of metals are preferably used II. To IV. Main group and the I. and II. As well as IV. To VIII. Subgroups in question, whereby copper, zinc, manganese, magnesium, Tin, iron and nickel may be mentioned as examples.

Suitable anions of salts are those which are preferably derived from the following acids: hydrohalic acids, such as, for example, hydrochloric acid and hydrobromic acid, and also phosphoric acid, nitric acid and sulfuric acid.

The metal salt complexes of compounds of formula (I) can be obtained in a simple manner by conventional methods, e.g. by dissolving the metal salt in alcohol, e.g., ethanol and adding to the compound of formula (I). Metal salt complexes can be prepared in a known manner, for example by Filter off, isolate and, if necessary, by Umkristall-I i sation cleaning.

The compounds of formula (I) can also be obtained by adding 3,3-dimethyl-1-fluoro-1-phenoxy-2-butanone (ole) the formula

RO - (Cj) - 0-CH-AC (CH _{3) 3} (V) ^ -f ρ

in soft

A and R have the meaning given above,

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in the melt at 100 to 20O ⁰ C with 1,2,4-triazole, or by reacting the compounds of the formula (V) with alkali metal salts of 1,2,4-treazole in an organic solvent, such as acetonitrile, at temperatures between 20 and 100 ⁰ C converts. Compounds of the formula (I) in which A represents the CH (OH) grouping can also be obtained by first converting the keto derivatives of the formula (V) in the manner indicated above to the corresponding keto derivatives of Formula (I) is implemented and then the keto group is reduced as described above (compare the details of this process variant according to DE-OS 30 31 846 CLeA 20 5033).

The 3,3-Dimet hy 1-1-fluor-1-phenoxy-2-butanone (oIe) der Formula (V) are obtained by adding halogen-ketones to the formula

Shark '- CH - CO - C (CH ₃ ) ₃ (VI)

F.
in which

Hal ^{1 stands} for chlorine or bromine,

with phenols of formula (III) in the presence of an inert organic solvent, such as acetone and in the presence of an acid binder, such as potassium carbonate, at temperatures between 20 and 100 ⁰ C is reacted; and, if appropriate, then reduced the keto group as described above (compare the information in DE-OS 30 31 846 CLeA 20 5033).

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/ Ib

The halogen-ketones of the formula (VI) are obtained by in 1-bromine (chlorine> -3,3-dimethyl-2-butanone the Shape L

(Cl) Br- CH ₂ - CO - C (CH ₃ ) ₃ (VII)

the bromine (chlorine) exchanges for fluorine in the usual way and in the resulting 3,3-dimethyl-1-fluoro-2-butanone the formula

F - CH ₂ - CO - C (CH ₃ ) ₃ (VIII)

one of the two active hydrogen atoms in usual Way exchanged for bromine (chlorine).

In some cases it can be beneficial to

to prepare certain compounds of the formula (I) by that one inventive compounds of the formula

HO '(XJ) - 0 - CH - CO -C (CH ₃ ) ₃ (Ia)

if N
N L-

in a known manner with a corresponding halide, such as an alkenyl halide, alkynyl halide, benzyl halide or Phenoxymethylhalogenid, in the presence of an inert organic solvent, such as acetone and in the presence of an acid binder, such as potassium carbonate, at temperatures between 20 and 100 ⁰ C. implements.

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The compound of the formula (Ia) can also be obtained by customary saponification of the corresponding 4-acetoxy derivative with sodium hydroxide solution can be obtained.

The active ingredients according to the invention have a strong microbiide effect and can combat undesirable Microorganisms are practically used. The active ingredients are for use as pesticides suitable.

Fungicidal agents in crop protection are used ^to control Plasmodiphoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes. Deuteromycetes.

The good plant tolerance of the active ingredients in the for combating plant diseases from above ground Parts of plants, of vegetation and seeds, and of the soil.

As a plant protection agent according to the invention Active ingredients with particularly good success for combating cereal diseases, such as Erysiphe graminis, Cochliobolus sativus. Rust, Pyrenophora teres and snow mold on grain, also of Venturia species, such as Venturia inaequalis, and rice diseases, such as Pellicularia sasakii and Pyricularia oryzae, can be used.

It should be emphasized that the substances according to the invention are not only have a protective effect, but partially are also systemically effective. In this way it is possible to protect plants against fungal attack if you have the active ingredients over the Soil and the root or, via the seeds, the aboveground Parts of the plant.

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The active ingredients can be converted into the customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, foams, pastes, soluble Powders, granulates, aerosols, suspension emulsion concentrates, Seed powder, active ingredient-impregnated natural and synthetic substances, ultra-fine encapsulation in polymers Substances and in coating compounds for seeds, also in formulations with burning charges, such as smoking cartridges and cans, -Spiralen and others as well as ÜLV cold and warm mist formulations.

These formulations are produced in a known manner, e.g. by mixing the active ingredients with extenders, that is, liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate .using surface-active agents, i.e. emulsifiers and / or dispersants and / or foaming agents. If water is used as an extender, organic solvents, for example, can also be used can be used as auxiliary solvents. As a liquid Solvents are essentially possible: aromatics, such as xylene, toluene, or alkyl I-naphthalenes, chlorinated Aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents, such as dimethylformamide and dimethyl sulfoxide, as well as water; Liquids with liquefied gaseous extenders or carriers are such liquids meant which are gaseous at normal temperature and under normal pressure, e.g. aerosol propellants, such as Halogenated hydrocarbons as well as butane, propane, nitrogen

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and carbon dioxide j as solid carriers come into question: For example, natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals such as finely divided silica, aluminum oxide and silicates; Solid carriers for granules are: for example broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules made from inorganic and organic flours and granules made from organic material such as sawdust, coconut shells, corn cobs and Tobacco stalks; As emulsifying and / or foam-forming agents there are suitable: for example nonionic and anionic emulsifiers, such as fatty acid ester _{Polyoxyethyien-5} polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates; Possible dispersants are: e.g. lignin sulphite waste liquors and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-like polymers can be used, such as Gum arabic, polyvinyl alcohol, polyvinyl acetate.

Dyes such as inorganic pigments, e.g. iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, Copper, cobalt, molybdenum and zinc can be used.

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The formulations generally contain between 0.1 and 95 percent by weight active ingredient, preferably between 0 and 90 p.

The active compounds may be present in the formulations or in the various use forms as a mixture with other known active compounds, such as fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth factors, plant nutrients and soil ^ J ₀ structure improvers.

The active ingredients can be used as such, in the form of their formulations or the application forms prepared therefrom by further dilution, such as ready-to-use solutions, Emulsions, suspensions, powders, pastes and granulates can be used. The application happens in the usual Way, e.g. by pouring, dipping, spraying, atomizing, atomizing, vaporizing, injecting, silting up, spreading, Dusting, scattering, dry pickling, moist pickling, wet pickling, slurry pickling or encrusting.

When treating parts of plants, the drug concentrations can be varied over a wide range in the application forms. They generally lie between 1 and 0.0001 weight percent, preferably between 0.5 and 0.001 58.

In the treatment of seeds, amounts of active compound of 0.001 to 50 g per kilogram of seed, preferably 0.1 UI to 10 g, are generally required.
When treating the soil, active substance concentrations of 0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% by weight, are required at the site of action.

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Manufacture of lung games
Example 1

CH ₂ = CH - CH ₂ - O - (Cj) - O -CH -CO -C (CH ₃ ) ₃

N -.1

(with preliminary product)

16.7 g (0.1 mol) Triazo LyLpinakoLiη and 8.2 g (0.1 mol) sodium acetate are dissolved in 100 mL glacial acetic acid and 16.01 g (0.1 mol) bromine are added dropwise at 45 ° C. It is allowed to stir for 20 minutes until the Br ₂ decolorization is complete, then poured into ice water and extracted with methylene

chloride. The organic phase is washed over sodium bicarbonate solution until neutral and at 40 ⁰ C concentrated in vacuo residual crude 1-bromo-3,3-Dimet hyl-1- (1, 2,4-triazol-1-yl) -butan-2 -one in 40 ml of acetonitrile and treated at 20 ⁰ C under stirring to a solution of 15g

(0.1 mol) 4-ALLyLoxyphenoL and 10.2g (0.1 mol) triethyL-amine in 18OmL acetonitrile. A
Slightly exothermic reaction. The reaction mixture is allowed to stir under reflux for 30 minutes. After cooling, it is poured into water, extracted with methylene chloride and washed

the organic phase with dilute hydrochloric acid. After this

Concentration in vacuo, the residue is stirred with cyclohexane and sucked off. 22 g (70% of theory) 1- (4-ALLyLoxyphenoxy) -3,3-dimethyL-1- (1,2,4-triazol-1-yL) -2-butanone are obtained from a melting point of 66 ° C.

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At game L 2

OH CH ₂ = CH-CH ₂ -0- <O) -0 -CH -CH -C (CH ₃ ) ₃

7.2 g (0.023 mol) 1- (4-Al LyLoxyphenoxy) -3,3-dimet hy 1-1 (1,2,4-triazol-1-yL) -2-butanone (Example 1) are dissolved in 80 ml of methanol added in portions with stirring at 2O ⁰ C and 1 g (0.027 mol) of sodium borohydride. The mixture is left to stir for 1 hour and. then concentrated in vacuo by distilling off the solvent. The residue is partitioned between methylene chloride / water. The organic phase is separated off, dried over sodium sulfate and concentrated in vacuo. 7 g (97.2% of theory) 1- (4-allyloxyphenoxy) -3,3-dimethyl-1- (1,2,4-triazol-t-yl) -2-butanol with a melting point of 85 ° are obtained C.

In an analogous manner and in accordance with the specified process conditions the compounds of the general formula listed in the table below

RO - (O) - ° - CH - A - C (CH ₃ ) ₃ (I)

obtain:

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Ex. F Jr. R CH ₂ - A. CO ; Melting point 3 ; CH ₃ Co- CH ₂ - CO CH (OH) Oil 4th H 2 " CO CO 204 5 CH = IC-CH ₂ - 2 " CO CH (OH) 97 6th CH Ξ C-CH ₂ - CH (OH) CO 96-100 7th ; CH ₂ = C (CL) - CO CH (OH) 60 8th CH ₂ = C (CL) - CH (OH) 68-70 9 Xl
Cl - ^ - O-CH CO resin 10 CL- ^ y-O-CH CH (OH) resin 11th (CH ₃ ) ₃ C-CH ₂ -C (CH ₃ ) ₂ -CH ₂ -CH = CH-CH ₂ -CO Oil 12th CF ₃ 68 13th CF ₃ 112 14th _CL ^ ..- _CH2 - 58-60 15th CLi [J-CH ₂ - 138-40 16 CH ₃ -C (CL) = CH-CH ₂ - Oil 17th CH ₃ -C (CL) = CH-CH ₂ - 69-72

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In the examples below, they will appear below specified compounds as comparison substances used:

CL O-CH-CO-

CL / N.

• N

OH

(B) Br- (C>"0-CH-CH-C (CH ₃ )

¹ - 'ι

N Il

(C) CL - ^ (._ / - 0-CH-C0-C (CH ₃ ) 3

Il

CH ₂ -NH-CS-S ^ _n

: d) I zn

CH ₂ -NH-CS-S'- "

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Example A.

Erysiphe test (barley) / protective

Solvent: 100 parts by weight of dimethylformamide Emulsifier: 0.25 part by weight of alkylaryl polyglycol ether

For the production of an appropriate preparation of the active substance 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier and the mixture is diluted Concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are sprayed with the preparation of active compound dew-moist. To When the spray coating dries on, the plants are dusted with spores of Erysiphe graminis f.sp.hordei.

The plants are placed in a greenhouse at a temperature of approx. 20 ^° C. and a relative atmospheric humidity of approx. 80% in order to promote the development of powdery mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, for example, the compounds according to the following preparation examples: 6, 1, 2, 7, 8, 10 and 12 show a clear superiority in effectiveness compared to the prior art.

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Example: B.

CochLioboLus sativus test (barley) / protektiν

Solvent: 100 parts by weight of dimethyl formamide Emulsifier: 0.25 parts by weight of alkylaryl polyglycol ether

For the production of an appropriate preparation of the active substance

1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for protective effectiveness, young plants are sprayed with the preparation of active compound dew-damp. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Cochliobolus sativus. The plants remain for 48 hours at 20 ^° C. and 100 % rel. Humidity in an incubation cabin.

The plants are placed in a greenhouse at a temperature of about 20 ^° C. and a relative humidity of about 80%.

Evaluation is carried out 7 days after the inoculation.

In this test, e.g. the compounds according to the following preparation examples: 5, 6, 1, 2, 7 and 8.

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Example C

Venturia test (apple) / protective

Solvent: 4.7 parts by weight acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

For the production of an appropriate preparation of the active substance 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier and diluted the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are sprayed with the active compound preparation until they are dripping wet. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the apple scab pathogen (Venturia inaequalis) and then remain ^{in an incubation cabin at 20 °} C. and 100% relative humidity for 1 day.

The plants are then placed in the greenhouse at 20 ^° C. and a relative atmospheric humidity of about 70%.

Evaluation is carried out 12 days after the inoculation.

A clear superiority in effectiveness compared to the prior art show in this test z.3. the compounds according to the following preparation examples: 7, 8 and 12.

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3example D

Pellicularia test (rice)

Solvent: 12.5 parts by weight acetone

Emulsifier: 0.3 part by weight of ALkyLaryLpoLygLykolether

For the production of an appropriate preparation of the active substance 1 part by weight of active ingredient is mixed with the stated amount of solvent and the concentrate is diluted Water and the specified amount of emulsifier to the desired Concentration.

To test their effectiveness, young rice plants in the 3 to 4 leaf stage are sprayed dripping wet. The plants remain in the greenhouse until they have dried off. The plants are then inoculated with Pellicularia sasakii and placed at 25 ^° C. and 100% relative humidity.

Evaluation is carried out 5 to 8 days after the inoculation

the disease infestation. |

A clear superiority in effectiveness against - s

above the state of the art show in this test, for example \

the compounds according to the following preparation examples: i ^:

12, 13 and 16. ' \

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Claims (1)

Claims M Λ Phenoxytriazolyl ketones and carbinols in general my formula ^R "° ~ \ Q / ~ O-CH-AC (CH ₃ ) ₃ (I) H J] in soft A stands for the keto group or the CH (OH) group and 4 R for hydrogen, alkenyl, alkynyl, haloalkyl, haloalkenyl, Alkylcarbonyl, optionally substituted Benzyl or optionally substituted phenoxymethyl stands, as well as their acid addition salts and metal salt complexes 2. Compounds of formula (I) in claim 1, wherein A for the keto group or the CH (OH) group stands, and R for hydrogen, for straight or branched chain Alkynyl with 2 to 6 carbon atoms, for haloalkyl with 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms represents haloalkenyl having 2 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, for alkylcarbonyl with 1 to 4 Carbon atoms in the alkyl part, as well as for each Le A 22 320 COPY egg because if necessary in the phenyl part one to three times, identically or differently through halogen, alkyl having 1 to 2 carbon atoms, nitro and haloalkyl substituted with 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms Benzyl or phenoxymethyl. 3. Compounds of formula (I) in claim 1, wherein A stands for the keto group or the CH (OH) group, and TO ^R f ^represents hydrogen, straight-chain or branched alkynyl having 3 to 12 carbon atoms, straight-chain or branched alkinyl having 3 to 4 carbon atoms, trifluoromethyl, substituted by chlorine ■ alkenyl having 3 or 4 carbon atoms, acetyl, Ehtylcarbonyl and in each case optionally in the phenyl moiety or benzyl or phenoxymethyl which is twice, identically or differently substituted by fluorine, chlorine and / or methyl. 4. Process for the preparation of phenoxytriazolyl ketones and carbinols of the general formula (I) N Li in which A stands for the keto group or the CH <OH) group and α COPY Le A 22 320 R for hydrogen, alkenyl, alkynyl, Ha I ogena I kyI, halogen alkenyl, A I ky I carbonyI, optionally substituted Benzyl or optionally substituted phenoxymethyl I stands, characterized in that one halotriazolylpinacoline of the formula Hal -CH-CO- CCCH ₃ ) ₃ (I ₁ ) N I] in which Hal represents fluorine, chlorine or _O rom, are reacted with phenols of the formula has the meaning given above, in the presence of a diluent and in the presence ■ converts J5 of an acid binding agent; and optionally also the keto derivatives obtained in this way Formula (I) reduced in the usual way by known methods, and furthermore, if appropriate, a subsequent addition to the compounds of the formula (I) thus obtained 2Q acid or a metal salt added. Le A 22 320 GOPY * t * W W 5. Fungicidal agents, characterized in that they contain at least one phenoxytriazolyl ketone or carbinol of the formula (I) in claims 1 and 4. 6. A method of combating fungi, characterized in that one phenoxytriazolyl ketones or carbinols of formula (I) in claims 1 and 4, can act on fungi or their habitat. 7. Use of phenoxytriazolyl ketones or carbinols of the formula (I) in claims 1 and 4 for Fight against fungi. 8. Use of phenoxytriazolyl ketones or carbinols of the formula (I) in Claims 1 and 4 as a plant protection agent. 9. Process for the preparation of fungicidal agents, characterized in that one phenoxytriazolyl ketones or carbinols of the formula (I) in claims 1 and 4, with extenders and / or surface-active Means mixed up. Le A 22 320